And ebenezer emmet reid



Patented Jan. 7, 1930 UNITED STATES PATENT OFFICE GLARENCE'I. IB. HENNING AND CHARLES E. BURKE, OF WILMINGTON, DELAWARE, AND EIBENEZEB EMMET REID, OF BALTIMORE, MARYLAND, ASSIGNORS TO E. I. DU' PONT DE NEMOURS & COMPANY, OF WILMINGTON, DELAWARE, A CORPORATION OF DELAWARE vanmsn NoIDrawing. Original application filed September 24, 1924, Serial 120.73%),689. Divided, and this application filed July 30, 1928. Serial No. 296,410.

the neutral salts having the following general graphical formula:

where R represents an alkyli 0r aryl radical preferably not containing more than one ring of carbon atoms such, for example, as methyl (CH,- ethyl (G I-I cyclo-hexyl (C H benzyl (C H etc.; M represents the radical of a heavy metal such as iron, zinc, manganese, etc.; and x stands for the number of eiiective valencies of said metal.

By the expression heavy metal we mean to include, in addition to the'metals mentioned above, copper, tin, lead, mercury, nickel, cobalt, silver, gold, and platinum and their equivalents.

Compounds of this general type may be readily prepared by intimately mixing an aqueous solution of the sodium salt ofthe monoalkyl phthalic acid with a solution of a soluble salt of a corresponding heavy metal, in which case the metal phthalic ester precipitates and can be separated from the supernatant liquid. If desired the compounds so prepared can be'further purified by dissolving'in ether, filtering any insoluble residue and then distilling off the ether.

The ferrous and ferric neutral salts of the monoalkyl esters of phthalic acid (such as the salts of the nebutyl ester) are brownish red compounds; the corresponding zinc, mercurous,mercur1c, plumbous, and stannous salts are colorless; the corresponding manganous and nickel (ous) salts are greenish; and the corresponding cobaltous and cupric salts are blue. All. these salts exist, at least initially, in the form of viscous oils, except the manganese and copper salts, which are crystalline at ordinary room temperatures. The ferric and mercuric salts are somewhat unstable, and the plumbous and stannous salts'are also unstable at ordinary temperatures in the presence of water. The zinc salt is unstable at temperatures above 100 C.

The colors of the iron, cobalt, and nickel salts of the monoalk l esters of phthalic acid, and the colors of lms, such as nitrocellulose films, containing these salts, are remarkably fast to both visible and ultra-violet light.

I We have discovered that compounds of this type are soluble in many organic solvents such as ether and acetone, and render available an excellent method of intimately incorporating compounds containing the heavy metals with other organic substances where they may function, for example as drying agents inpaints and varnishes, or as catalytic agents in the carrying out of other chemical reactions, as for example, hydrogenation.

As an example of the use of one of these organo-metallic compounds 'as a drier in varnish, the following example might be given:

China wood oil 5O gals. Linseedoil 12.5 gals. Rosin 120 lbs. Turpentine 125 gals. Cobalt butyl phthalateul 1.22 lbs.

plication Serial No. 739,689filed September 24, 1924. We claim:

1. An oil type varnish containing a salt of a member of the group which consists of iron, zinc, manganese, copper, tin, lead, mercury, nickel, cobalt, silver, gold, and platinum and a monoalkyl ester of phthalic acid which salt issoluble in acetone.

2. An oil type Varnish containing a salt of a member of the group which consists of iron, zinc, manganese, copper, tin, lead,

mercury, nickel, cobalt, silver, gold, and platinum and the butyl half ester of phthalic acid which salt is soluble in acetone.

3. An oil type varnish containing the cobalt salt of the butyl halfester of phthalic acid which is soluble in acetone.

4. An oil typ'e varnish in which the drier is a salt of a member of the group which consists of iron, zinc, manganese, copper, tin, lead,

mercury, nickel, cobalt, silver, gold, and platinum and a monoalkyl ester of phthalic acid which salt is soluble in acetone.

5. An oil type varnish in which the drier is a a salt of a member of the group which consists of iron, zinc, manganese, copper, tin, lead, mercury, nickel, cobalt, silver, gold, and platinum and the butyl half ester of phthalic acid which salt is soluble in acetone.

6. An oil type varnish in which the drier is 5 the cobalt salt of the butyl half ester of phthalic acid which is soluble in acetone.

7. A varnish containing China wood oil, linseed oil, rosin, turpentine and a salt of a member of the group which consists of iron,

so zinc, manganese, copper, tin, lead, mercury, nickel, cobalt, silver, gold, and platinum and a monoalkyl ester of phthalic acid which salt is soluble in turpentine and oil.

8. A varnish containing China wood oil,

linseed oil, rosin, turpentine and a salt of a member of the group Which consists of iron, zinc, manganese, copper, tin, lead, mercury, nickel, cobalt, silver, gold, and platinum and the butyl half ester of phthalic acid which 4o salt is soluble in turpentine and oil;

9. A varnish containing China wood oil, linseed oil, rosin, turpentine and the cobalt salt of the butyl half ester of phthalic acid which is soluble'in turpentine and oil. In testimony whereof we aflix our signatures. v

CLARENCE I. B. HENNING. CHARLES E. BURKE. EBENEZER EMRIET REID. 

